What we’re talking about

A one-on-one is a regularly recurring discussion between you and someone who works directly below you: if you’re running a small business, we’ll assume that’s an employee. It’s not a formal meeting or a work check-in. Instead, the idea is to give a platform for your employee to communicate with you on topics that are important to them. Every one or two weeks, at an agreed day and time, you give space (typically 30 to 45 minutes) for an employee to ask in-depth questions, highlight any issues they’re having and receive guidance on their strengths and weaknesses. Or even for them to talk about personal problems that are on their mind – it’s really up to them. This is their meeting, not yours. 

Why it’s important

Regular communication is essential to build a genuine relationship on an individual level with someone who’s working for you – and for you to show that you’re committed to them developing and growing. This might seem more relevant for big companies with loads of employees and line managers, but it’s just as critical for small businesses, too. A report by analytics firm Gallup shows that employees who meet with their managers are three times as likely to be engaged in their jobs. 

One-on-ones are mutually beneficial. Employees know they have the space to air their opinions, thoughts and problems about anything and everything. Employers, meanwhile, get to better understand their employees: their strengths and weaknesses, what they need and how to best treat them in terms of allocating work. It can also end up saving you time as daily interruptions can be saved for that weekly meet.

Things to note

Your behavior is super important. How you conduct yourself is crucial to productive one-on-ones. Canceling, for example, sends a negative message. You shouldn’t approach this like a meeting but as an opportunity to get to know someone better. Remove any distractions, don’t fill in gaps and practice active listening. And try not to invite your ego to this one. 

It should be employee-led. It’s generally pretty hard to communicate upwards in the employer-employee relationship – so this is time and space for them to talk. A general rule for structuring the chat should be: the first third of the time for the employee to speak; the second third where you speak; then the final third where you both discuss the future. 

They need to have regular cadence. Scheduling your one-on-ones on a calendar to repeat might seem unrealistic with the changeable nature of running a business, but it needs to be done. For your employee to reap the benefits of a continuous dialog, they need to know that this is important to you and will happen on an ongoing basis. It also gives them adequate time to prepare, too – even if you do end up rescheduling them nearer the time. 

They’re not just about work. One of the dangers of regular chats – particularly when they’re all about current work tasks – is that they become repetitive and stale, and then get pushed to one side. That’s why it’s important to talk about high-level stuff besides their tasks. Like feedback they have on how the business is progressing, their personal development, and career goals, ie, subjects that are explored on an ongoing basis, with long-term goals. 

How to carry out a productive one-on-one

1. Decide on the length and frequency. Work out what makes sense and is achievable for you based on your schedule and number of employees. If you have a lot of employees, a bi-weekly meeting might make more sense. Two weeks should be the maximum time between meetings, and 30 minutes should be the minimum length. Equally, junior employees might benefit more from a weekly meeting than experienced employees who are more settled. Whatever you decide upon, it needs to be something you can stick with and commit to going forward. 

2. Explain what you’re doing with your team. Communicate with all of your employees in advance, focusing on why you’re doing one-on-ones and outline how they’ll actually work in practice. Make clear that this is their platform and space to use as they see fit – and not just for updates on projects and tasks. Since the onus is on them, provide a list of thought starters. That might include challenges they’ve faced or concerns they have; their current job focus and interests; roadblocks; the culture within the team; and how they’d like to grow.

3. Find a time. Secure a slot in the week that works for both you and your employee and is unlikely to get pushed back or cancelled. For example, Monday mornings aren’t usually the one, as the week’s to-do list can often dominate your thoughts. Put it as a recurring event in your calendars. 

4. Find a place. Decide where you’re going to do it. The location for your one-on-one needs to be somewhere where you both feel comfortable (and is convenient for your workday in general). That might be in a public space, like a cafe; a walk and chat; a place where you have a little bit of privacy in your workplace; or done remotely. It doesn’t have to always be the same and it can be a good chance to break up the day and change things up.

5. Come prepared. Before your chat, review any previous notes you might have made about that employee, and note topics or areas you want to speak to them about. During the week, you should be jotting down bullet points or questions to ask on a document. This can then become a running summary of your meetings with the employee, where you also note takeaways and actionable to-dos at the end of each session. 

6. Give them the floor. Conduct your one-on-one following the structure above, letting the employee talk first. If they talk for longer than you’d anticipated, let it happen. Be flexible with your agenda. When it comes to your turn to talk, ask what they need from you and what you can improve upon. Touch on those same overarching topics as mentioned in Step 2, and try to finish with an element of coaching where you can give them tips or feedback on how they can improve in certain areas. And always finish on a positive or affirming note. 

7. Agree on some action items. At the end of the chat, make any relevant action items clear, so both you and the employee know what you’ll do before the next one. That means you won’t be starting again from scratch and the next meeting can pick up naturally from where you left off. Your doc should have an ongoing log of the major topics and points that you can constantly refer back to – and use to understand whether they’re being improved upon.  

Key takeaways

The main purpose of a one-on-one is to build a strong relationship between you and your employee – not to discuss work projects. 

This is all about giving space – and a platform – to your employee to talk about the things they want to talk about, no matter what they might be. 

It needs to be organized for a recurring time and loosely structured. Trying to do it ad-hoc will result in it falling by the wayside and not benefiting either party. 

Level up

Example. For ideas on questions you can ask your employee, check out this list from Soapbox.

Tool. To really level up your meeting game, Fellow helps you keep on track of topics, create templates, action items and pretty much anything else that goes into conducting a good meeting. 

Perspective. Front co-founder Mathilde Collin shares how she approaches her one-on-ones in this insightful blogpost.  

Perspective. The Manager Tools podcast has a whole series dedicated to one-on-ones – getting pretty granular on how to get them right.